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Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A
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2012 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 32, 6504-6512 p.Article in journal (Refereed) Published
Abstract [en]

An important feature of the synthesis of salinosporamide A. a potent proteasome inhibitor, is the establishment of the quaternary stereocenter at C3. A new route has been developed based on the methylation of a functionalized pyrrolidinone. Direct methylation reaction led to the unwanted diastereomer: however, by means of a Corey-Chaykovsky reaction followed by LiAlH4 epoxide opening, the desired alcohol was obtained. The pyrrolidinone was elaborated through a key allylation reaction between a tertiary allyltitanium reagent and an aldehyde bearing a spiroketal moiety in alpha-position.

Place, publisher, year, edition, pages
2012. Vol. 68, no 32, 6504-6512 p.
Keyword [en]
Salinosporamide, Hoppe allylation, Pyrrolidinone, Methylation reaction, Corey-Chaykovsky reaction
National Category
Organic Chemistry
URN: urn:nbn:se:su:diva-80630DOI: 10.1016/j.tet.2012.05.103ISI: 000306267800014OAI: diva2:556466
Swedish Research Council


Available from: 2012-09-25 Created: 2012-09-25 Last updated: 2012-09-28Bibliographically approved

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Santoro, StefanoHimo, Fahmi
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Department of Organic Chemistry
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